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3,3'-Dicarboxybenzidine

HCID 16475
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Basic information

CAS
2130-56-5
Standard SMILES
Nc1ccc(-c2ccc(N)c(C(=O)O)c2)cc1C(=O)O
InChIKey
IIQLVLWFQUUZII-UHFFFAOYSA-N
Molecular formula
C14H12N2O4
Average molar mass
272.26 g/mol
Monoisotopic mass
272.07970687

Names & identifiers

Preferred name
3,3'-Dicarboxybenzidine
IUPAC
2-amino-5-(4-amino-3-carboxyphenyl)benzoic acid
English name
4,4'-DIAMINOBIPHENYL-3,3'-DICARBOXYLIC ACID
Molecular formula
C14H12N2O4
Molecular weight
272.26

Names & synonyms

2130-56-5Benzidine-3,3'-dicarboxylic acid4,4'-diaminobiphenyl-3,3'-dicarboxylic acid5,5'-Bianthranilic acid5,5'-Dianthranilic acid3,3'-Benzidinedicarboxylic acidBenzidine-M,M'-dicarboxylic acid3,3'-dicarboxy-4,4'-diaminobiphenyl3,3'-DICARBOXYBENZIDINEPLU8S18T9FHSDB 27384,4'-Diamino-3,3'-biphenyldicarboxylic acid
Show more names
5,5’-dianthranilicacid5,5’-bianthranilicacid3,3’-dicarboxybenzidinekwasbenzydynodwukaroksylowy3,3’-benzidinedicarboxylicacidbenzidine-m,m’-dicarboxylicacid3,3′-dicarboxyl-4,4′-diaminobiphenyl4,4’-diamino-3’-biphenyldicarboxylicacid
EINECS 218-348-9Kwas benzydynodwukaroksylowy [Polish]3,3'-Biphenyldicarboxylic acid, 4,4'-diamino-Kwas benzydynodwukaroksylowyBRN 2815505DTXSID4062195(1,1'-Biphenyl)-3,3'-dicarboxylic acid, 4,4'-diamino-[1,1'-Biphenyl]-3,3'-dicarboxylic acid, 4,4'-diamino-

Database identifiers

CAS
2130-56-5
PubChem CID
16475
DTXSID
DTXSID4062195
ChEMBL
CHEMBL1584156
UNII
PLU8S18T9F
EC Number
218-348-9
Nikkaji
J36.112G

Properties

Computed structural properties

XLogP
2.3
Topological polar surface area
127 Ų
Hydrogen bond donors
4
Hydrogen bond acceptors
6
Rotatable bonds
3
Heavy atoms
20
Formal charge
0
Complexity
351

Experimental & physicochemical properties

Chemical ClassesNitrogen Compounds -> Benzidine and Derivatives
Color/FormWhite crystals
Solubility · 2 items

Sol in alcohol, ether; insol in water

>40.8 [ug/mL] (The mean of the results at pH 7.4)

DecompositionWhen heated to decomp it emits toxic fumes of /nitrogen oxides/.
Physical DescriptionWhite solid; [HSDB]

Physicochemical properties

Melting point
300 °C · 300°C
Boiling point
415.31 °C · 415.31°C (rough estimate)
Density
1.2499 · 1.2499 (rough estimate)
refractive index
1.618 · 1.6180 (estimate)
storage temp.
2 · 2-8°C, protect from light
pka
2.07 · 2.07±0.10(Predicted)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

Hazard information

Hazards SummarySome evidence for carcinogenicity in rodents when dosed subcutaneously; Emergency treatment: Methemoglobinemia; [HSDB] See Benzidine.

Toxicology

Adverse EffectsMethemoglobinemia - The presence of increased methemoglobin in the blood; the compound is classified as secondary toxic effect
Non-Human Toxicity Excerpts · 1 item

3,3'-BENZIDINE DICARBOXYLIC ACID (BDC) SUBCUTANEOUSLY ADMIN TO RATS ONCE A WEEK AT 20 MG FOR 18 MO & TO MICE ONCE A WK AT 5 MG FOR 20.5 MO & WITH FOOD AT 2 MG SIX TIMES WEEKLY HAD A CARCINOGENIC EFFECT, ESP ON THE LIVER OF MICE & ON THE BLOOD FORMING ORGANS, GLANDULAR SECTION OF STOMACH & MAMMARY GLANDS OF RATS. BDC AND ITS SODIUM SALT WERE MUCH LESS CARCINOGENIC THAN BENZIDINE, O-TOLUIDINE BENZIDINE, & 3,3'-DICHLOROBENZIDINE, SUGGESTING THAT THE ABILITY OF AN ORTHO CARBOXYL GROUP TO FORM HYDROGEN BONDS WITH THE AMINO GROUP REDUCES THE FREE RADICAL & BLASTOMOGENIC EFFECTS OF BENZIDINE DERIVATIVES.

Probable Routes of Human Exposure · 1 item

Processes in which dried dye is handled have the greatest potential for employee exposure during the manufacture or repackaging of benzidine-based dyes. ... During use of benzidine-based dyes, the greatest potential for exposure would be expected to be among dye-weighers who handle dry powders. /Benzidine-based dyes/

Antidote and Emergency Treatment · 2 items

Basic treatment: Establish a patent airway. Suction if necessary. Watch for signs of respiratory insufficiency and assist ventilations if needed. Administer oxygen by nonrebreather mask at 10 to 15 L/min. Monitor for pulmonary edema and treat if necessary ... . Monitor for shock and treat if necessary ... . Anticipate seizures and treat if necessary ... . For eye contamination, flush eyes immediately with water. Irrigate each eye continuously with normal saline during transport ... . Do not use emetics. For ingestion, rinse mouth and administer 5 ml/kg up to 200 ml of water for dilution if the patient can swallow, has a strong gag reflex, and does not drool ... . Cover skin burns with dry sterile dressings after decontamination ... . /Poison A and B/

Chemistry & industry

Uses & manufacturing

Uses · 3 items

Used to make copper azo dyes; [HSDB]

Dyestuff

Used for the manufacture of azo dyes containing copper

Methods of ManufacturingBy boiling meta-nitrobenzaldehyde with caustic soda, reducing with zinc dust and acidifying.
General Manufacturing Information[1,1'-Biphenyl]-3,3'-dicarboxylic acid, 4,4'-diamino-: INACTIVE

Applications

Uses4,4'-DIAMINOBIPHENYL-3,3'-DICARBOXYLIC ACID is used as a monomer for the synthesis of COF materials.

Upstream & downstream products

Upstream raw materials

2-Nitrobenzoic acidZINC

Downstream products

[1,1'-Biphenyl]-3,3'-dicarboxylicacid,4-[2-[1-hydroxy-6-(phenylamino)-3-sulfo-2-naphthalenyl]diazenyl]-4'-[2-(1-hydroxy-5-sulfo-2-naphthalenyl)diazenyl]-,sodium salt (1:4)tetrasodium [mu-[4,4'-bis[[6-(3-carboxyanilino)-1-hydroxy-3-sulpho-2-naphthyl]azo][1,1'-biphenyl]-3,3'-dicarboxylato(8-)]]dicuprate(4-)

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Compound notes

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On this pageBasic informationNames & identifiersPropertiesSafety & regulationChemistry & industryRelated reactionsCompound notes
color
Needles
InChI
InChI=1S/C14H12N2O4/c15-11-3-1-7(5-9(11)13(17)18)8-2-4-12(16)10(6-8)14(19)20/h1-6H,15-16H2,(H,17,18)(H,19,20)
InChIKey
IIQLVLWFQUUZII-UHFFFAOYSA-N
SMILES
C1(C2=CC=C(N)C(C(O)=O)=C2)=CC=C(N)C(C(O)=O)=C1
FDA UNII
8 S18T9F · PLU8S18T9F
EPA Substance Registry System
1 · [1,1'-Biphenyl]-3,3'-dicarboxylic acid, 4,4'-diamino- (2130-56-5)
Symbol(GHS)
7 · GHS07
Signal word
Warning
Hazard statements
302 · H302-H315-H319-H335
Precautionary statements
261 · P261-P280-P301+P312-P302+P352-P305+P351+P338
TSCA
TSCA listed
Hazardous Substances Data
2130 · 2130-56-5(Hazardous Substances Data)
Toxicity
100 mmol/L · pic-esc 100 mmol/L MDMIAZ 31,11,79

Advanced treatment: Consider orotracheal or nasotracheal intubation for airway control in the patient who is unconscious, has severe pulmonary edema, or is in respiratory arrest. Positive pressure ventilation techniques with a bag valve mask device may be beneficial. Monitor cardiac rhythm and treat arrhythmias as necessary ... . Start an IV with D5W /SRP: "To keep open", minimal flow rate/. Use lactated Ringer's if signs of hypovolemia are present. Watch for signs of fluid overload. Consider drug therapy for pulmonary edema ... . For hypotension with signs of hypovolemia, administer fluid cautiously. Watch for signs of fluid overload ... . Treat seizures with diazepam (Valium) ... . Use proparacaine hydrochloride to assist eye irrigation ... . /Poison A and B/

Safety data

tsca
TSCA listed
Toxicity
pic-esc 100 mmol/L MDMIAZ 31,11,79
Signal word
Warning
Symbol(GHS)
GHS07
Hazard statements
H302-H315-H319-H335
Precautionary statements
P261-P280-P301+P312-P302+P352-P305+P351+P338
Hazardous Substances Data
2130-56-5(Hazardous Substances Data)
Direct Brown 186
Direct blue 126 (C.I. 34010)
[1,1'-Biphenyl]-3,3'-dicarboxylic acid, 4-[(6-carboxy-1,7-dihydroxy-3-sulfo-2-naphthalenyl)azo]-4'-[(4,5-dihydro-3-methyl-5-oxo-1-phenyl-1H-pyrazol-4-yl)azo]-, tetrasodium salt
[1,1'-Biphenyl]-3,3'-dicarboxylic acid, 4-[[4,5-dihydro-3-methyl-5-oxo-1-(6-sulfo-2-naphthalenyl)-1H-pyrazol-4-yl]azo]-4'-[[1-[[(2-methoxyphenyl)amino]carbonyl]-2-oxopropyl]azo]-, trisodium salt