3,4-Diaminobenzamide - ≥95% , CAS No.7005-37-0

CAS: 7005-37-0 Cat. No.: D1350248 Summenformel: C₇H₉N₃O Molekulargewicht: 151.17 EG-Nummer: 840-028-8 PubChem CID: 21217843

GRADE & PURITY ≥95%

Storage

Room temperature

Shipped In

Normal

Specifications

Spezifikationen & Reinheit

≥95%

Storage

Room temperature

Verschickt in

Normal

Reinheit

≥95%

Namen und Kennungen

Kanonisches Lächeln

C1=CC(=C(C=C1C(=O)N)N)N

IUPAC Name

3,4-diaminobenzamide

InChIKey

RGJXMMUQTCONEI-UHFFFAOYSA-N

INCHI

1S/C7H9N3O/c8-5-2-1-4(7(10)11)3-6(5)9/h1-3H,8-9H2,(H2,10,11)

Isomere SMILES

C1=CC(=C(C=C1C(=O)N)N)N

PubChem CID

21217843

Molekulargewicht

151.17

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Klasse Benzene and substituted derivatives
      • Subclass Benzoic acids and derivatives
        • Ebene5 Aminobenzoic acids and derivatives
          • Ebene6 Aminobenzamides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Klasse: Benzene and substituted derivatives
• Subclass: Benzoic acids and derivatives
• Intermediate Tree Nodes: Aminobenzoic acids and derivatives
• Direct Parent: Aminobenzamides
• Alternative Parents: Benzamides Benzoyl derivatives Aniline and substituted anilines Primary carboxylic acid amides Amino acids and derivatives Primary amines Organooxygen compounds Organic oxides Hydrocarbon derivatives
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Aminobenzamide - Benzamide - Benzoyl - Aniline or substituted anilines - Amino acid or derivatives - Primary carboxylic acid amide - Carboxamide group - Carboxylic acid derivative - Primary amine - Organooxygen compound - Organonitrogen compound - Amine - Organic oxygen compound - Organic nitrogen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Beschreibung: This compound belongs to the class of organic compounds known as aminobenzamides. These are organic compounds containing a benzamide moiety with an amine group attached to the benzene ring.
• 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

Chemische und physikalische Eigenschaften

• Molekulargewicht: 151.170 g/mol
• XLogP3: -0.500
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 1
• Exact Mass: 151.075 Da
• Monoisotopic Mass: 151.075 Da
• Topological Polar Surface Area: 95.100 Ų
• Heavy Atom Count: 11
• Formal Charge: 0
• Complexity: 160.000
• 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 tested bioassay or immunoassay protocols are specified for this item. For synthetic applications, follow standard organic chemistry procedures corresponding to the transformation of interest (see Reaction Conditions and Synthetic Utility). For preparation of assay stocks, dissolve in DMSO or acidic aqueous media as appropriate, filter (0.22 μm), and dilute into the assay buffer while monitoring for precipitation.

Biological Roles

• Item-specific biological/biochemical role: None specified; this reagent is offered for research and synthetic use.

• General context (literature)

  • 3,4-Diaminobenzamide is not a known endogenous metabolite. As a polyfunctional aniline/benzamide, it can serve as a scaffold in medicinal chemistry campaigns to probe H-bonding and anilide–arene interactions in enzyme or receptor binding sites.
  • The adjacent diamine permits formation of chelating diimines/heterocycles (e.g., quinoxalines) that are frequently encountered in probe and lead-like libraries.
  • Protonation behavior: in acidic environments, formation of mono- or di-protonated ammonium species increases aqueous solubility, which can be leveraged for biochemical assay stock solutions; however, actual biological activity, ADME, or safety endpoints are beyond the scope here and are not claimed.

Research Use Note: For research use only. No medical, diagnostic, or clinical use is intended or implied.

Buffer Applications

This compound is not a buffering agent and does not form defined buffer systems in typical laboratory ranges. If aqueous handling is required (e.g., for assay stocks), dissolve in minimal DMSO/DMF or acidify water (e.g., dilute HCl or acetate buffer) to form soluble ammonium salts, then adjust conditions for the downstream application. For pH control, use established buffers such as phosphate, acetate, or HEPES as appropriate to your assay.

Green Alternatives

• Solvent choices (comparative, general)

  • Replace DMF/NMP where possible with EtOAc, 2-MeTHF, CPME, propylene carbonate, or water/ethanol systems for condensations.
  • Acid-catalyzed condensations to quinoxalines often proceed in ethanol or acetic acid, sometimes even under aqueous micellar conditions (literature) — reducing dipolar aprotic solvent use.

• Reagent economy

  • Use catalytic acid (AcOH, p-TsOH) rather than stoichiometric mineral acids when feasible.
  • CDI for urea formation avoids phosgene derivatives; aqueous nitrite under flow can improve safety during diazotization.

• Energy efficiency

  • Microwave or sealed-tube short-time heating can cut reaction times and energy consumption for condensations and acylations.

• Waste minimization

  • Protect–deprotect steps can be reduced by leveraging innate chemoselectivity (e.g., transient protonation of one aniline to select for the other in electrophilic N-acylations).

Small comparison (general)

• Conventional: DMF/NMP, benzene/toluene; strong mineral acids; stoichiometric coupling reagents.
• Greener: 2-MeTHF/EtOAc/ethanol/water; organic acids; catalytic coupling platforms or recyclable reagents.

Note: Selection must be validated for the specific transformation and purity targets.

Pharmaceutical Uses

• Item-specific pharmacopeial/excipient status: Not specified for this item; refer to CoA/Spec Sheet.

• General context (non-clinical)

  • 3,4-Diaminobenzamide is primarily a synthetic intermediate/building block in discovery and process chemistry. The diamine motif enables rapid heterocycle assembly (e.g., quinoxalines) and N-derivatization for SAR exploration.
  • It is not typically used as a finished excipient. When incorporated in route design, attention is paid to control of aromatic amine impurities and nitrosamine risk assessments in line with current regulatory guidance.

No therapeutic or clinical claims are made. For any GMP or regulatory use, qualify the material to your internal specifications and applicable pharmacopeial/ICH guidelines.

Physical Properties

• Item-specific specifications

  • Appearance: Not specified for this item; refer to CoA/Spec Sheet.
  • Grade/Purity: Not specified for this item; refer to CoA/Spec Sheet.

• Literature/typical properties (for context; not item specifications)

  • Physical state: typically a crystalline solid (aromatic amide with two anilines).
  • Acid–base character: contains two basic aniline nitrogens (weak bases) and one amide (non-basic, weakly acidic at the NH). Expect formation of stable salts in strong mineral acids.
  • Solubility tendencies: appreciable solubility in polar aprotic solvents (DMSO, DMF, NMP) and hot alcohols; limited to moderate solubility in water at neutral pH, improved in acidic media via ammonium salt formation.
  • UV/Vis: aromatic chromophore with strong UV absorption in the 200–300 nm region (literature generality for anilides).
  • Hydrogen-bonding: tri-functional H-bond donor/acceptor matrix (amide C=O acceptor; amide NH donor; two aniline NH donors), enabling strong lattice energies and specific solvation.

• Computed/estimation notes

  • LogP is expected to be low-to-moderate for an anilide with two amines (literature qualitative expectation: polar aromatic). Exact values are not specified for this item; refer to CoA/Spec Sheet.
  • Melting point, density, refractive index: Not specified for this item; refer to CoA/Spec Sheet.

Quality and Grades

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

• Interpreting common grades (general guidance)

  • Research grade: suitable for most synthetic and screening work; assay typically reported on CoA by NMR/LC.
  • Purified/98%+: appropriate for route scouting and SAR; minimizes byproduct carryover in multistep sequences.
  • HPLC grade (for solvents) is not applicable to this solid reagent; for solids, low-residual-solvent and low-inorganic content are more relevant.

• Stabilizers and implications

  • No stabilizer is indicated for this item. For polyfunctional anilines, stabilizers are rarely used; quality is primarily preserved by dryness, protection from air/light, and appropriate packaging.

• What to check on receipt (practical tips)

  • Appearance and color: polyaromatic amines can darken on air exposure; slight tan coloration does not necessarily indicate impurity but verify by NMR/LC.
  • Identity confirmation: 1H/13C NMR in DMSO-d6 or CD3OD, HRMS, and LC/HPLC purity. Two aniline NH signals may be broad and solvent/temperature dependent; amide NH typically appears downfield (DMSO-d6).
  • Water content and residual solvents: Not specified for this item; refer to CoA/Spec Sheet.

Reaction and Applications

• Building-block roles

  • Adjacent (3,4-) diamine motif enables formation of fused heteroaromatics via condensation with 1,2-dicarbonyl compounds to give quinoxaline derivatives (the amide remains as a pendant group, providing further diversification or directing effects).
  • Two anilines serve as handles for selective protection (Boc, Cbz, sulfonyl) and diversification (acylation, urea/thiourea, sulfonamide formation), while the amide can be transformed (e.g., activation to acid chloride equivalent then further coupling if hydrolysis to acid is performed upstream).

• Typical transformations (literature/general)

  • Quinoxaline synthesis: condense with glyoxal, diketones (e.g., benzil) or α-dicarbonyls under acid catalysis or thermal conditions in alcohols/acetic acid.
  • Diazotization/azo coupling: each aniline can be diazotized (NaNO2/HCl, 0–5 °C) to form diazonium salts for azo coupling or Sandmeyer-type diversification (requires careful control due to multiple amines).
  • Electrophilic aromatic substitution: highly activated ring permits rapid EAS (nitration, sulfonation) but regioselectivity is influenced by the opposing directing effects of the amide (meta) vs amines (ortho/para); protection may be required.
  • N-derivatizations: urea/thiourea formation with CDI/thiocarbonyldiimidazole; sulfonamides with sulfonyl chlorides; carbamates with chloroformates.

• Practical tips

  • Chemoselectivity control: protect one aniline (e.g., Boc) to differentiate reactivity; amide NH is far less nucleophilic but can still acylate under forcing conditions.
  • For condensations, pre-form the diammonium salt in acetic acid to increase solubility, then heat to drive water removal.
  • Monitor by LC-UV at 254/280 nm; multi-UV maxima common for anilide chromophores.

Reaction Conditions

General literature guidance for transformations involving 3,4-diaminobenzamide (optimize per substrate):

• Quinoxaline formation

  • Reagents: 1,2-dicarbonyl (e.g., glyoxal, benzil).
  • Solvent: ethanol, acetic acid, or EtOH/AcOH (1:1); water/ethanol under acid catalysis also reported.
  • Conditions: 60–120 °C (reflux) for 1–12 h; catalytic AcOH or p-TsOH. Remove water (Dean–Stark in higher-boiling alcohols) to drive equilibrium.
  • Workup: neutralize, concentrate, and crystallize or purify by chromatography.

• N-Acylation / sulfonylation (selective on anilines)

  • Reagents: acyl/sulfonyl chlorides (1.0–1.2 equiv per targeted NH), base (DIPEA, pyridine, Na2CO3).
  • Solvent: DCM, THF, EtOAc, or DMF.
  • Temperature/time: 0 °C to rt, 0.5–4 h. Protect one amine if mono-selectivity is required.

• Carbamate/urea formation

  • Reagents: chloroformates (for carbamates); CDI or triphosgene-alternatives for ureas.
  • Solvent: THF, DCM, or DMF; base as needed.
  • Conditions: 0–40 °C, 1–6 h.

• Diazotization/azo coupling (handle with care)

  • Reagents: NaNO2, mineral acid (HCl) at 0–5 °C to form diazonium salts; couple with activated aromatics.
  • Safety: perform at low temperature; avoid accumulation of dry diazonium salts; consider flow for improved control.

• Analytical monitoring

  • LC-UV at 254/280 nm; LC-MS in ESI+ (readily protonated). TLC with basic modifier in eluent to prevent streaking.

Yields depend on substrates and protection strategies; consult primary literature for target-specific optimization.

Safety and Handling

• GHS/SDS

  • Signal word, hazard statements, pictograms, and classification: Not specified for this item; refer to the product SDS for authoritative information.

• General hazards for aromatic diamines and benzamides (literature/general guidance)

  • Aromatic amines can cause skin/eye irritation and may be harmful if swallowed or inhaled. Dust may be irritating to the respiratory tract. Handle as a potentially sensitizing amine.
  • Avoid contact with oxidizing agents and strong electrophiles (e.g., acylating/sulfonylating reagents) unless intentionally reacting under controlled conditions.

• Recommended PPE and engineering controls

  • Use lab coat, safety glasses, and appropriate chemical-resistant gloves (e.g., nitrile). Handle solids in a fume hood to minimize dust exposure. Employ local exhaust ventilation during weighing and charging.

• First-aid overview (general)

  • Inhalation: move to fresh air; seek medical attention if symptoms persist.
  • Skin/eye contact: rinse with plenty of water for at least 15 minutes; remove contaminated clothing; seek medical advice for persistent irritation.
  • Ingestion: rinse mouth; do not induce vomiting; seek medical attention.

• Storage incompatibilities and stability

  • Keep tightly closed, dry, and away from strong oxidizers and strong acids/bases when not in use. Protect from prolonged light and moisture to prevent degradation or discoloration common to anilines.

Always consult the current SDS and your institutional safety protocols before use.

Solvent Selection

3,4-Diaminobenzamide is a polar, hydrogen-bonding solid. Solvent choice is driven by reaction chemistry and desired ionization state.

• Miscibility/solubility tendencies (general)

  • High: DMSO, DMF, NMP; improved solubility on gentle heating.
  • Moderate: ethanol, methanol, isopropanol (often enhanced at reflux or with acidification).
  • Low at neutral pH: water; markedly higher in aqueous mineral acid via diammonium salt formation.
  • Limited in nonpolar solvents (toluene, hexanes); use co-solvents or convert to salts/derivatives for processing.

• Selection by task

  • Couplings/acylations/sulfonylations: use dry DMF, DCM, THF, or acetonitrile with base (DIPEA, pyridine). For greener options, consider 2-MeTHF or EtOAc when compatible.
  • Condensations with 1,2-dicarbonyls (quinoxaline formation): ethanol, acetic acid, or n-butanol; water or ethanol/water under catalytic acid can also be effective.
  • Salt handling/purification: dissolve in dilute HCl or acetic acid, then re-basify for precipitation.

• Comparison snapshot (general)

  • DMSO vs DMF: DMSO often gives higher solubility; DMF may simplify workup. Both are strong hydrogen-bond acceptors aiding dissolution of multi-N substrates.
  • Alcohols vs aprotics: alcohols facilitate azeotropic water removal in condensations; aprotics favor clean acylations with reduced side hydrolysis.

Dry solvents are advisable for moisture-sensitive derivatizations (e.g., isocyanate formation), while protic media suit salt handling and condensations.

Storage and Reconstitution

• Storage (from Product Data)

  • Store at room temperature.
  • Shipped under normal conditions.

• General storage guidance

  • Keep tightly sealed in the original container, protected from light and moisture. Minimize headspace and repeated air exposure to limit oxidative discoloration typical of anilines.

• Reconstitution and stock solutions

  • Solubility: readily dissolves in DMSO, DMF, or NMP; moderate in alcohols (heat if needed). Limited in neutral water; dissolve in dilute HCl or AcOH to form soluble ammonium salts when aqueous handling is required.
  • Typical stock preparation: 10–100 mM in dry DMSO or DMF; filter through 0.22 μm PTFE/NYLON to clarify. For aqueous stocks, prepare in 0.1–0.5 M AcOH or 0.01–0.1 M HCl, then adjust final assay conditions by dilution.
  • Stability: prepare fresh solutions when possible; store aliquots at 2–8 °C for short term or −20 °C for longer term to limit degradation. Avoid repeated freeze–thaw of solutions.

• Specifications such as water content, residual solvents, or stabilizers: Not specified for this item; refer to CoA/Spec Sheet.

Research Use Note: For research use only.

Structure and Identity

3,4-Diaminobenzamide is an aniline-rich benzamide bearing two adjacent (ortho to each other) amino groups on the aromatic ring.

• Item identifiers (from Product Data)

  • SKU: D1350248
  • CAS: 7005-37-0
  • CID: 21217843
  • InChIKey: 315727 (as provided)
  • SMILES: Not specified for this item; refer to CoA/Spec Sheet.

• Literature structural data (for reference; not item-specific specifications)

  • Molecular formula: C7H9N3O (literature)
  • Molecular weight: ~151.17 g/mol (literature)
  • A representative SMILES often reported: O=C(N)c1ccc(N)c(N)c1 (literature)

• Structural features (descriptive)

  • Core: benzamide (–CONH2) attached to a phenyl ring.
  • Substituents: two ring –NH2 groups at the 3- and 4-positions relative to the amide carbonyl (the two –NH2 are ortho to each other).
  • Functional groups: one amide (primary), two anilines (primary aromatic amines).
  • Resonance/activation: the ring is strongly activated by the two electron-donating anilines; the amide is moderately deactivating/meta-directing, creating distinctive regioselectivity patterns in EAS.
  • 2D description: a six-membered aromatic ring bearing, consecutively, para and meta amino groups and a benzamide at the reference position; no stereocenters, planar conjugated system involving the amide and ring.

Synthetic Utility

• Functional-group reactivity

  • Two aniline –NH2 groups: nucleophilic toward acyl, sulfonyl, and chloroformate electrophiles; can be diazotized; form imines/Schiff bases under dehydrating or catalytic conditions.
  • Amide –CONH2: largely non-nucleophilic; can participate in H-bonding and direct EAS; can be hydrolyzed to the corresponding acid under strong acidic/basic conditions for further transformations.

• Direction in aromatic substitution

  • Strong ortho/para-directing effect from each –NH2 competes with meta-directing amide; protection strategies (e.g., Boc/Alloc) often used to control regiochemistry.

• Heterocycle construction

  • Quinoxalines: condensation with 1,2-diketones/α-dicarbonyls.
  • Diimine ligands: condensation with dialdehydes to give chelating scaffolds.

• Divergent synthesis strategies

  • Sequential N-functionalization: differentiate the two anilines via temporary protection or by protonation state control; employ stepwise acylation to access unsymmetrical derivatives.
  • Late-stage diversification of the benzamide (after ring functionalization) via hydrolysis–re-coupling can broaden analogue space.

• Purification and analytics

  • Many derivatives remain polar; normal-phase silica with basic modifiers (e.g., 1–2% Et3N) or reverse-phase preparative LC are effective. Monitor by LC-MS and multi-wavelength UV for sensitivity.

Target Specificity

Not applicable. This product is a small-molecule reagent, not a biological affinity reagent or antibody. No target, epitope, clone, or species reactivity is defined for this item.