3-Hydroxy-1,1-dimethylurea - ≥95% , CAS No.52253-32-4

CAS: 52253-32-4 Cat. No.: H996353 Formula: C₃H₈N₂O₂ Peso molecolare: 104.110 Numero EC: 984-027-1

GRADE & PURITY ≥95%

Storage

Room temperature

Specifications

Specifiche e purezza

≥95%

Condizioni di conservazione di stoccaggio

Room temperature

Purezza

≥95%

Nomi e identificatori

Sorrisi canonici

CN(C)C(=O)NO

IUPAC Name

3-hydroxy-1,1-dimethylurea

InChIKey

SJIIGPWRRLKCEI-UHFFFAOYSA-N

INCHI

1S/C3H8N2O2/c1-5(2)3(6)4-7/h7H,1-2H3,(H,4,6)

Peso molecolare

104.110

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organic acids and derivatives
    • Classe Organic carbonic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organic acids and derivatives
• Classe: Organic carbonic acids and derivatives
• Subclass: Not available
• Intermediate Tree Nodes: Not available
• Direct Parent: Organic carbonic acids and derivatives
• Alternative Parents: Organopnictogen compounds Organonitrogen compounds Organic oxides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aliphatic acyclic compounds
• Substituents: Carbonic acid derivative - Organic nitrogen compound - Organic oxygen compound - Organopnictogen compound - Organic oxide - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Carbonyl group - Aliphatic acyclic compound
• Descrizione: This compound belongs to the class of organic compounds known as organic carbonic acids and derivatives. These are compounds comprising the organic carbonic acid or a derivative thereof.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Proprietà chimiche e fisiche

• Peso molecolare: 104.110 g/mol
• XLogP3: -0.900
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 104.059 Da
• Monoisotopic Mass: 104.059 Da
• Topological Polar Surface Area: 52.600 Ų
• Heavy Atom Count: 7
• Formal Charge: 0
• Complexity: 71.300
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 1

Application Protocols

No manufacturer‑verified experimental protocols are provided for this item.

General starting points (literature/general; adjust to your system):

• Preparation of an O‑acyl hydroxamate:
  • Dissolve 3‑Hydroxy‑1,1‑dimethylurea in dry DCM (0.1–0.2 M). Add DIPEA (2–3 equiv) and catalytic DMAP. Cool to 0–5 °C. Add acid chloride (1.1–1.5 equiv) dropwise. Stir at 0–25 °C until complete (TLC/LC‑MS). Quench with sat. NaHCO3, extract, dry, concentrate, and purify by silica gel chromatography.
• Mitsunobu O‑alkylation (if compatible):
  • In dry THF or 2‑MeTHF, combine the alcohol substrate, triphenylphosphine, and DIAD/DEAD at 0 °C; then add a solution of the N‑hydroxy urea. Warm to rt and stir until completion. Work up by aqueous quench and chromatography.
• Stock solution preparation (for assay derivatization work):
  • Prepare 10–100 mM solutions in DMSO or DMF. Filter (0.22 µm) if particulates are present. Store aliquots at room temperature protected from moisture; confirm stability by LC‑MS.

Note: These are generic literature‑style procedures for N‑hydroxy substrates and are not validated for this specific SKU. Optimize stoichiometry, temperature, and solvent based on your substrates and desired selectivity.

Biological Roles

Item-specific biological/biochemical roles: Not specified for this item; refer to primary literature if needed for contextual studies.

General context (literature/general; not specific to this SKU):

• N‑Hydroxy ureas are structural relatives of hydroxylamines and hydroxamic acids, which are known for metal‑binding and as intermediates in biochemical derivatization. However, biological roles depend strongly on substitution and are not generalizable.
• Physicochemical profile (high polarity, H‑bonding) suggests potential for aqueous compatibility in assay development or derivatization workflows, but no biological activity should be inferred.
• Research positioning: Useful as a functional handle (N–OH) for generating probes (e.g., hydroxamates for metal coordination in enzyme studies) strictly for in‑vitro research.

Compliance note:

• This product is supplied for research use only. It is not intended for food, drug, household, or diagnostic applications. No clinical or therapeutic claims are made or implied.

Buffer Applications

This compound is not a buffering agent and is not typically used to make defined pH buffer systems. Its urea/N‑hydroxy functionality does not provide a well‑defined pKa pair suitable for classical buffering ranges.

Practical note (research context):

• If used in biochemical assays, prepare stock solutions in water, aqueous alcohols, or DMSO/DMF as appropriate, and add to pre‑made buffers (e.g., phosphate, HEPES, Tris) rather than relying on the compound to contribute to buffering capacity.
• Verify compound stability in the chosen buffer (pH‑dependent hydrolysis and O‑acylation/oxidation should be considered). Actual stability data for this item are not specified; perform small‑scale tests.

Green Alternatives

Perspective: The compound itself is a polar, non‑volatile organic solid/liquid (exact appearance not specified). “Green” considerations therefore center on solvent/reagent choices and process design rather than substitution of the compound.

Greener choices in typical transformations (literature/general):

• O‑Acylation to hydroxamates:
  • Prefer coupling reagents like CDI or EDC (with catalytic DMAP) in greener solvents (ethyl acetate, 2‑MeTHF) over acid chlorides in chlorinated solvents.
  • Employ enzyme‑mediated acylations or aqueous micellar catalysis when compatible with substrate stability.
• O‑Alkylation:
  • Use greener solvents (ethanol, water/ethanol, 2‑MeTHF) and benign leaving groups; consider phase‑transfer catalysis to avoid polar aprotics where possible.
• Workup/waste:
  • Minimize chlorinated solvents; opt for EtOAc/hexane or EtOAc/MeOH systems for extraction and chromatography.
  • Recycle solvent streams and use in‑process controls to reduce over‑reagent use.

Mini comparison (general, illustrative):

• THF vs 2‑MeTHF: 2‑MeTHF (biorenewable, higher bp, easier phase separation) can substitute for THF in many acylation/alkylation steps; beware of differing solubility and water content management.
• DCM vs EtOAc: Ethyl acetate provides lower toxicity and better biodegradability; ensure adequate solubility and control of exotherms in acylations.

Note: No specific process data for this SKU are provided. Validate greener substitutions at small scale to confirm chemoselectivity and yield.

Pharmaceutical Uses

Item-specific pharmacopeial status and excipient roles: Not specified for this item; there is no provided information indicating any pharmacopeial listing or approved excipient function.

General formulation context (literature/general):

• Urea derivatives can, in some cases, serve as hydrogen‑bonding co‑formers in cocrystals or as derivatization handles for pro‑moieties in medicinal chemistry discovery. N‑hydroxy groups are versatile for forming hydroxamates and related motifs during lead optimization.
• For preclinical research only: If employed in screening libraries or as a synthetic intermediate, ensure residual levels and impurity profiles meet internal research specifications. Avoid any implication of therapeutic or clinical utility.

Regulatory note:

• For research use only. Not for use in humans or animals. No claims of safety or efficacy are made or implied for clinical or diagnostic applications.

Physical Properties

Item-specific specifications: Not specified for this item; refer to CoA/Spec Sheet.

General physicochemical expectations (literature/general; non‑spec for this SKU):

• Phase/appearance: Urea derivatives of this polarity and size are typically low‑melting solids or waxy semi‑solids; exact appearance for this item is not specified.
• Polarity and hydrogen bonding: Strongly polar due to the urea carbonyl and N–OH. Capable of both H‑bond donation (N–OH, possibly NH if present in tautomeric balance) and acceptance (C=O, N–O).
• Solubility (qualitative): Often readily soluble in polar protic solvents (water, methanol, ethanol) and polar aprotic solvents (DMSO, DMF). Limited solubility is expected in nonpolar hydrocarbons. Actual solubility limits for this item are not specified.
• Volatility: Very low; urea derivatives are essentially non‑volatile under ambient conditions.
• Acid/base behavior: The N‑hydroxy functionality can show weak acidity (O–H) and engage in tautomerism/hydrogen bonding; urea nitrogens are weak bases at best. No pKa values are specified for this item.
• Stability notes: N‑hydroxy ureas are generally stable under neutral conditions but can undergo O‑acylation/alkylation and may slowly hydrolyze or decompose under strong acid/base or prolonged heating. Light/air sensitivity is typically low, though prolonged exposure to strong oxidants/reductants should be avoided.

For numeric values (mp, bp, density, refractive index, logP, pKa): Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

Item-specific grade/purity for this SKU: Not specified for this item; refer to CoA/Spec Sheet.

Guidance on interpreting typical grades for urea derivatives (general):

• Research grade: Suitable for most synthetic and screening work. Trace impurity profiles (water, residual solvents, metals) are not tightly controlled beyond standard QC. If this item is supplied as research grade, verify suitability for moisture‑sensitive or catalytic applications.
• Analytical/AR grade: Tighter control of assay and common impurities; may be preferred for quantitative analytical workflows involving derivatization.
• High‑purity or >98% assay: Minimizes side reactions in O‑acylation/alkylation chemistry and reduces background in mechanistic or kinetics studies.
• Stabilizers: Not specified for this item; refer to CoA/Spec Sheet. N‑hydroxy ureas typically do not require stabilizers, but moisture control can be relevant.

What to check on the CoA for this compound type:

• Identity confirmation: 1H/13C NMR (diagnostic N–OH signal), IR (strong amide C=O near 1650–1700 cm⁻¹; N–O stretch), MS.
• Assay/purity and residual solvents.
• Water content (e.g., Karl Fischer) if your application is moisture‑sensitive.
• Inorganic residues/metals: Usually low relevance for small organics unless used in metal‑catalyzed steps; not specified for this item.
• UV profile: Only critical if used in photochemical or analytical UV workflows; not specified for this item.

Reaction and Applications

Manufacturer application text: Not provided for this item. The following are general considerations for N‑hydroxy urea derivatives and should be treated as literature/general guidance.

Representative applications (literature/general):

• O‑Acylation to hydroxamic acids: The N–OH group can be selectively O‑acylated with activated carboxylic acids (acid chlorides/anhydrides or coupling reagents) to furnish O‑acylated products (hydroxamates), useful as ligands or intermediates.
• O‑Alkylation: Under suitable conditions (e.g., Mitsunobu or SN2 with strong leaving groups), formation of O‑alkyl oxime‑like ethers from the N–OH moiety is feasible.
• Electrophilic activation: Carbamoyl functionality can participate in hydrogen‑bonding catalysis or as a directing group in selective transformations of adjacent functions (context‑dependent).
• Protecting group chemistry: N‑hydroxy ureas can act as masked hydroxylamine equivalents; the O‑substituent can be unveiled under reductive or hydrolytic conditions.

Practical notes:

• Chemoselectivity: O‑acylation typically dominates over N‑acylation for N‑hydroxy substrates with proper base and temperature control; sterics from the N,N‑dimethyl group further disfavor N‑acylation at that nitrogen.
• Bases/activators: Use mild, non‑nucleophilic bases (DIPEA, pyridine) and coupling agents (EDC/HOBt, HATU) when acid chlorides are unsuitable.
• Moisture control: While not extremely moisture‑sensitive, coupling efficiency benefits from dry solvents and anhydrous conditions.
• Workup: O‑acylated products may be acid‑labile; avoid strong mineral acids during quench if undesired deacylation is a concern.

Note: No item‑specific validated applications are provided; users should optimize conditions for their substrates.

Reaction Conditions

Item-specific, validated conditions: Not specified for this item; users should optimize based on substrate and desired transformation.

General conditions for common transformations of N‑hydroxy ureas (literature/general):

• O‑Acylation to hydroxamates:
  • Solvents: DCM, THF, MeCN, DMF, or 2‑MeTHF (anhydrous).
  • Bases: Pyridine, triethylamine, DIPEA; catalytic DMAP for rate enhancement.
  • Reagents: Acid chlorides/anhydrides, or EDC/EDC•HCl with HOBt/HOAt or HATU.
  • Temperature: 0–25 °C (control exotherm); times 0.5–12 h depending on substrate.
• O‑Alkylation:
  • Mitsunobu (PPh3/DIAD) in THF/THF‑alternatives at 0–25 °C, or SN2 with alkyl halides/tosylates under phase‑transfer or in polar aprotics with base (NaH, K2CO3) as compatible.
• O‑Sulfonylation/Phosphorylation:
  • Use sulfonyl chlorides or POCl3‑derived reagents with base in DCM/MeCN at 0–25 °C; monitor by TLC/LC‑MS.

Monitoring and workup (general):

• TLC with polar eluents (EtOAc/hexanes or MeOH/DCM) or HPLC/LC‑MS due to polarity.
• Quench acylations with aqueous bicarbonate; avoid strong acid if the product is acid‑labile.
• Typical isolated yields for well‑matched systems: good to excellent (literature‑reported ranges often 60–90%); actual yields depend on substrate and conditions.

Caveats:

• Moisture can reduce coupling efficiency; ensure dry glassware and solvents.
• Strong bases may induce undesired N→O acyl migration or decomposition; prefer mild, non‑nucleophilic bases.

Safety and Handling

Authoritative safety data for this SKU are not specified in the Product Data. Always consult the product SDS for definitive information.

Item-specific (from Product Data):

• GHS classification: Not specified for this item; refer to SDS.
• Signal word / H‑statements / pictograms: Not specified for this item; refer to SDS.
• Storage conditions: Room temperature.

General safety guidance for N‑hydroxy urea derivatives (literature/general):

• Hazards: N‑hydroxy functionalities can be irritants to skin/eyes and may pose risks upon ingestion or inhalation of dusts. Avoid dust generation and contact with oxidizing agents or strong reducing agents. Thermal decomposition may release nitrogen oxides.
• PPE: Use lab coat, safety goggles, and suitable chemical‑resistant gloves (e.g., nitrile). Employ local exhaust ventilation when handling powders; avoid inhalation of dust.
• Incompatibilities: Strong acids/bases (can promote hydrolysis or decomposition), strong oxidizers (may over‑oxidize the N–OH), strong reducing agents (may reduce N–O). Avoid acyl halides without proper control due to exothermic O‑acylation.
• First aid (overview; refer to SDS for details):
  • Skin/eyes: Rinse with water for at least 15 minutes; remove contaminated clothing; seek medical attention if irritation persists.
  • Inhalation: Move to fresh air; provide oxygen if needed; seek medical attention if symptoms develop.
  • Ingestion: Rinse mouth; do not induce vomiting; seek medical attention.
• Fire response: Use water spray, CO2, dry chemical, or foam. Combustion may produce CO/CO2 and nitrogen oxides. Firefighters should wear self‑contained breathing apparatus.

Solvent Selection

Applicability: This is a polar, hydrogen‑bonding small molecule. Solvent choice will affect handling, reaction performance (e.g., O‑acylation), and crystallization.

General solvent behavior (literature/general):

• Polarity class: Polar protic and polar aprotic solvents are generally preferred.
• Likely miscibility: Good solubility in methanol, ethanol, isopropanol, DMSO, DMF, and possibly water; limited solubility in ethers and poor in hydrocarbons. Actual solubility limits for this item are not specified.
• Dielectric environment: Higher dielectric media (water, DMSO, DMF) can stabilize charged transition states in acyl transfer chemistry involving the N–OH group.

Practical selection tips:

• For stock solutions: DMSO or DMF enable high‑concentration solutions; filter‑sterilize if needed for biochemical assays (research use only).
• For O‑acylation to hydroxamates: Use a dry, polar aprotic solvent (DCM, THF, MeCN, DMF) with a mild base (e.g., pyridine, DIPEA) and controlled temperature.
• For recrystallization: Consider alcohol/water or alcohol/ether systems; screen based on small‑scale trials because specific solubilities are not specified for this item.

Comparison with alternatives (general):

• Versus less substituted N‑hydroxyurea: The N,N‑dimethyl substitution reduces basicity at the carbamoyl nitrogen and can alter solubility and selectivity in O‑ vs N‑acylation.
• Versus hydroxylamine salts: This neutral N‑hydroxy urea is easier to handle than hydroxylamine hydrochloride but is less nucleophilic; use stronger activators for O‑acylation when needed.

Storage and Reconstitution

Item-specific (from Product Data):

• Storage conditions: Room temperature.
• Shipped in: Not specified for this item; refer to CoA/Spec Sheet.
• Appearance: Not specified for this item; refer to CoA/Spec Sheet.

General guidance (literature/general):

• Container: Store tightly sealed in an inert, clean bottle (glass preferred) with a desiccant if ambient humidity is high; the compound is polar and can absorb moisture.
• Light/air: Ambient light is typically acceptable; avoid prolonged exposure to strong UV. Normal lab atmosphere is generally fine, but avoid oxidizing environments.
• Reconstitution/stock solutions:
  • For organic stocks: Dissolve in DMSO, DMF, methanol, or ethanol to the desired concentration. Filter if needed. Record exact solvent and concentration on the vial.
  • For aqueous use: If water solubility is adequate, prepare in deionized water or buffered media. Verify pH stability; adjust pH minimally to avoid decomposition.
• Freeze–thaw: Not typically required for solids or room‑stable liquids. If preparing solutions for extended storage, aliquot to avoid repeated freeze–thaw; many DMSO solutions are stable at room temperature for short periods, but confirm by analytical QC.

Shelf life: Not specified for this item; refer to CoA/Spec Sheet and perform periodic QC (NMR/LC‑MS) for long‑term projects.

Research use note: For research use only.

Structure and Identity

Brief overview: 3‑Hydroxy‑1,1‑dimethylurea is a urea-derivative in which the urea core is N,N-dimethyl‑substituted at one terminus and bears a hydroxy substituent at the opposite (the “3-”) position, consistent with an N‑hydroxy urea motif. This confers both hydrogen‑bond donor and acceptor capability and a highly polar character.

Item-specific (from Product Data):

• SKU: H996353
• Product name: 3‑Hydroxy‑1,1‑dimethylurea
• CAS: 52253‑32‑4
• PubChem CID: 354650
• InChIKey: 337479 (as provided)
• SMILES: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular formula: Not specified for this item; refer to CoA/Spec Sheet.
• Molecular weight: Not specified for this item; refer to CoA/Spec Sheet.

Structural features (chemistry description; interpretation from name, literature/general):

• Core functionality: urea (carbamoyl, –NH–CO–N–) bearing an N‑hydroxy group (N–OH) at the non‑dimethylated nitrogen.
• Substitution pattern: “1,1‑dimethyl” implies two methyl groups on the same urea nitrogen, generating a tertiary carbamamide center adjacent to an N‑hydroxy moiety.
• Functional groups: urea (amide-like), N‑hydroxyl (hydroxylamine‑like). Both groups enable chelating hydrogen bonding and strong polarity.
• 2D structure in words: a carbonyl carbon doubly bonded to oxygen and single‑bonded to two nitrogens; one nitrogen bears two methyl substituents, the other bears a hydroxyl group (N–OH). No rings, no stereocenters.

Note on nomenclature (literature/general): This connectivity is commonly described as N‑hydroxy‑N,N‑dimethylurea (an N‑hydroxyurea where the opposite nitrogen is N,N‑dimethyl‑substituted).

Synthetic Utility

Overview (literature/general): 3‑Hydroxy‑1,1‑dimethylurea, consistent with an N‑hydroxy‑substituted, N,N‑dimethylated urea, offers a bifunctional platform: a urea carbonyl (amide‑like) and an N‑hydroxy handle. This combination enables selective O‑functionalization while modulating basicity and sterics via the dimethyl substituents.

Key transformations:

• O‑Acylation to hydroxamates: Reaction with acid chlorides/anhydrides or via carbodiimide coupling (e.g., EDC/HOBt, HATU) delivers O‑acylated products. The dimethyl substitution disfavors competing N‑acylation at that nitrogen, often aiding selectivity.
• O‑Sulfonylation/Phosphorylation: Reaction with sulfonyl or phosphorochloridates affords O‑sulfonyl or O‑phosphoryl derivatives—useful as leaving groups or ligands.
• O‑Alkylation: Under Mitsunobu or SN2 conditions with activated electrophiles, providing oxime‑ether‑like products.
• Redox manipulation: The N–OH can engage in controlled oxidations (to N‑oxo species) or reductions (to secondary amide‑like forms), though conditions require care to avoid over‑reaction; optimize on small scale.

Retrosynthetic value:

• Serves as a masked hydroxylamine equivalent where the urea carbonyl tempers reactivity and can be retained or removed later depending on the sequence.

Practical advantages:

• Polar, easy‑to‑handle substrate; typically compatible with common polar solvents.
• Reduced volatility simplifies workup; crystallization or trituration often affords high purity.

Item-specific assay/impurity controls: Not specified for this item; consult the CoA/Spec Sheet for purity and identity data before use.

Target Specificity

Not applicable. This product is a small‑molecule reagent and has no antibody/biologic target specificity parameters.

Item-specific data such as antigen/epitope, clone, species reactivity, or isotype are not relevant and are not provided for this SKU.