3-Methyl-4-nitrobenzoic acid

HCID 18370CAS 3113-71-1

Basic information

Standard SMILES
Cc1cc(C(=O)O)ccc1[N+](=O)[O-]
InChIKey
XDTTUTIFWDAMIX-UHFFFAOYSA-N
Molecular formula
C8H7NO4
Average molar mass
181.15 g/mol
Monoisotopic mass
181.0375077

Overview

3-methyl-4-nitrobenzoic acid appears as needles or off white powder. (NTP, 1992)

Names & identifiers

Preferred name
3-Methyl-4-nitrobenzoic acid
IUPAC
3-methyl-4-nitrobenzoic acid
English name
3-Methyl-4-nitrobenzoic acid
Molecular formula
C8H7NO4
Molecular weight
181.15

Names & synonyms

3-Methyl-4-nitrobenzoic acid4-Nitro-m-toluic acidBenzoic acid, 3-methyl-4-nitro-m-Toluic acid, 4-nitro-4-nitro-3-methylbenzoic acidNSC 28455DTXSID1025641UNII-ELP258JXH0EINECS 221-479-4ELP258JXH0NSC-28455DTXCID305641
Show more names
4-Nitro-m-toluylsureMethyl-4-nitrobenzoicRMA-1094,3-NMBAFluralaner-027RARECHEM AL BO 0346-4-nitrobenzoic AcidFluralaner Impurity 48
M-METHYL-P-NITROBENZOIC ACIDMETHYL-4-NITROBENZOIC ACID, 3-RefChem:947703-methyl-4-nitrobenzoateBENZOIC ACID, 3-METHYL-4-NITROXDTTUTIFWDAMIX-UHFFFAOYSA-N3113-71-1MFCD00007168

Database identifiers

CAS
3113-71-1
PubChem CID
18370
DTXSID
DTXSID1025641
ChEMBL
CHEMBL1329280
UNII
ELP258JXH0
EC Number
221-479-4
Nikkaji
J208.697B

Properties

Computed structural properties

XLogP
2.4
Topological polar surface area
83.1 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
4
Rotatable bonds
1
Heavy atoms
13

Experimental & physicochemical properties

LogP2.42
Solubilityless than 1 mg/mL at 72 °F (NTP, 1992)
Melting Point421 to 424 °F (NTP, 1992)
Physical Description3-methyl-4-nitrobenzoic acid appears as needles or off white powder. (NTP, 1992)

Physicochemical properties

Melting point
216 · 216-218 °C (lit.)
Boiling point
314.24 °C · 314.24°C (rough estimate)
Density
1.4283 · 1.4283 (rough estimate)
refractive index
1.5468 · 1.5468 (estimate)
storage temp.
Sealed in dry,Room Temperature
solubility
slightly sol. in Alcohol

Safety & regulation

GHS classification

GHS Classification · 4 items

Warning

H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]

P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 82 reports by companies from 6 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

DOT LabelPoison
Fire HazardsFlash point data for this chemical are not available; however, it is probably combustible. (NTP, 1992)
Health HazardsExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Reactive GroupAcids, Carboxylic
Reactivity Profile · 1 item

3-METHYL-4-NITROBENZOIC ACID is a nitrated carboxylic acid. Carboxylic acids donate hydrogen ions if a base is present to accept them. They react in this way with all bases, both organic (for example, the amines) and inorganic. Their reactions with bases, called "neutralizations", are accompanied by the evolution of substantial amounts of heat. Neutralization between an acid and a base produces water plus a salt. Carboxylic acids with six or fewer carbon atoms are freely or moderately soluble in water; those with more than six carbons are slightly soluble in water. Soluble carboxylic acid dissociate to an extent in water to yield hydrogen ions. The pH of solutions of carboxylic acids is therefore less than 7.0. Many insoluble carboxylic acids react rapidly with aqueous solutions containing a chemical base and dissolve as the neutralization generates a soluble salt. Carboxylic acids in aqueous solution and liquid or molten carboxylic acids can react with active metals to form gaseous hydrogen and a metal salt. Such reactions occur in principle for solid carboxylic acids as well, but are slow if the solid acid remains dry.

Air and Water ReactionsInsoluble in water.

Safety & protection

Fire FightingFires involving this compound can be controlled with a dry chemical, carbon dioxide, or Halon extinguisher. (NTP, 1992)
First Aid · 1 item

EYES: First check the victim for contact lenses and remove if present. Flush victim's eyes with water or normal saline solution for 20 to 30 minutes while simultaneously calling a hospital or poison control center. Do not put any ointments, oils, or medication in the victim's eyes without specific instructions from a physician. IMMEDIATELY transport the victim after flushing eyes to a hospital even if no symptoms (such as redness or irritation) develop.

Nonfire Spill Response · 1 item

SMALL SPILLS AND LEAKAGE: Should a spill occur while you are handling this chemical, FIRST REMOVE ALL SOURCES OF IGNITION, then you should dampen the solid spill material with 60-70% ethanol and transfer the dampened material to a suitable container. Use absorbent paper dampened with 60-70% ethanol to pick up any remaining material. Seal the absorbent paper, and any of your clothes, which may be contaminated, in a vapor-tight plastic bag for eventual disposal. Solvent wash all contaminated surfaces with 60-70% ethanol followed by washing with a soap and water solution. Do not reenter the contaminated area until the Safety Officer (or other responsible person) has verified that the area has been properly cleaned.

Isolation and EvacuationExcerpt from ERG Guide 154 [Substances - Toxic and/or Corrosive (Non-Combustible)]:
Personal Protective Equipment (PPE) · 1 item

RECOMMENDED RESPIRATOR: Where the neat test chemical is weighed and diluted, wear a NIOSH-approved half face respirator equipped with an organic vapor/acid gas cartridge (specific for organic vapors, HCl, acid gas and SO2) with a dust/mist filter. (NTP, 1992)

Safety data

PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
hs_code
29163900
risk_code
36/37/38-20/21/22
Signal word
Warning

Chemistry & industry

Uses & manufacturing

General Manufacturing InformationBenzoic acid, 3-methyl-4-nitro-: ACTIVE
Applications · 3 items

DescriptionIn organic synthesis, 3-Methyl-4-nitrobenzoic acid (abbreviated as MNBA) is the fine chemical product that adds value is higher; many critical organic products are obtained for raw material can synthesize further with it, as 4-chloro-quinazoline-6-ethyl formate, 2-n-propyl-4-methyl-6-carboxy benzimidazole, 4-methyl-2-ethyl-1H-benzoglyoxaline-6-methyl-formiate, 3,4-dihydro-4-quinazoline is with-6-formic acid, 4-aminophenyl-1,3-dioctyl phthalate, 4-Amino-3-methylbenzoic acid methyl esters, 4-nitrophenyl-1,3-dioctyl phthalate etc. In medicine, it is an essential intermediate in the synthesis of telmisartan (via esterification, reduction, butyrylation, nitration, reduction and cyclization), which is used to treat essential hypertension. Telmisartan is a drug belonging to the group of antagonists of angiotensin II receptors. The active ingredient telmisartan counteracts the effect of angiotensin II, allowing the arteries to relax, thereby reducing blood pressure. As a precursor, pharmaceutical researchers have also synthesized anti-cancer substances and AIDS drugs with MNBA[1].

Uses3-Methyl-4-nitrobenzoic Acid is used as a reagent in the synthesis of influenza neuraminidase inhibitors with pyrrolidinobenzoic acid scaffold containing lipophilic side chains.

General DescriptionNeedles or off white powder.

Preparation methods · 1 item

Preparation3-Methyl-4-nitrobenzoic acid was synthesized via oxidation of 2,4-(dimethylnitrobenzene) with mole-(cular) oxygen catalyzed by cobalt acetate in acetic acid in the presence of an initiator.It was found that the yield of 3-methyl-4-nitrobenzoic acid increased remarkably with the addition of sodium bromide as a co-(catalyst).The reaction was carried out at 130 ℃ for 8 h at 0.8 MPa of oxygen in the presence of 0.017 mol of cobalt acetate,(0.017 mol) of sodium bromide,and 0.30 mol of 2-butanone with 1.00 mole of 2,4-dimethylnitrobenzene.(Under) these conditions 99% of the reactant converted with a selectivity of 52% to 3-methyl-4-(nitrobenzoic) acid,and the yield of 3methyl-4-(nitrobenzoic) acid was 51%.The reaction mechanism and the function of(sodium) bromide were discussed.According to the fact that the reaction could not proceed without the presence of an initiator,it was proposed that the reaction took place via a free radical mechanism,and(sodium) bromide reacted with Co(Ⅲ) to generate bromine radicals,which promoted the formation of benzyl radicals.Synthesis of 3-Methyl-4-nitrobenzoic Acid via Catalytic Oxidation with Molecular OxygenMethod for preparing 3-methyl-4-nitrobenzoic acid by oxidizing with nitric acid

Suppliers50 total

国药集团化学试剂有限公司86-21-63210123 · [email protected]
梯希爱(上海)化成工业发展有限公司021-67121386 · [email protected]
衢州润东化工有限公司0570-8789886 18892685668 · [email protected]
上海阿拉丁生化科技股份有限公司400-6206333 13167063860 · [email protected]
INTATRADE GmbH+49 3493/605464 · [email protected]

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