4-(Hydroxymethyl)benzoic acid

Base Information

• Chemical Name: 4-(Hydroxymethyl)benzoic acid
• CAS No.: 3006-96-0
• Molecular Formula: C8H8O3
• Molecular Weight: 152.15
• Hs Code.: 29181990
• European Community (EC) Number: 628-233-9
• UNII: 9Z28L8STHD
• DSSTox Substance ID: DTXSID40184111
• Nikkaji Number: J256.581A
• Wikidata: Q27273399
• ChEMBL ID: CHEMBL4636837
• Mol file: 3006-96-0.mol

Synonyms:4-(Hydroxymethyl)benzoic acid;3006-96-0;4-HYDROXYMETHYLBENZOIC ACID;4-Hydroxythylbenzoic acid;96937-45-0;4-(Hydroxymethyl)benzoicacid;Benzoic acid, 4-(hydroxymethyl)-;4-hydroxymethyl-benzoic acid;MFCD00017598;4-(hydroxymethyl)-benzoic acid;Benzoic acid, 4-hydroxymethyl-;UNII-9Z28L8STHD;9Z28L8STHD;CHEMBL4636837;HMBA Linker;58590-49-1;Enamine_005867;p-hydroxymethyl benzoic acid;Fenpyroximate M-16;p-Hydroxymethylbenzoic Acid;SCHEMBL49984;p-(hydroxymethyl)benzoic acid;P-CARBOXYBENZYL ALCOHOL;4-(Hydroxylmethyl)benzoic acid;Benzoic acid,4-(hydroxymethyl)-;DTXSID40184111;HMS1410K15;CS-CY-00024;BDBM50540780;CCG-49783;RB3326;4-(Hydroxymethyl)benzoic acid, 99%;.ALPHA.-HYDROXY-P-TOLUIC ACID;AKOS001053879;AC-3060;CS-W018100;IDI1_008102;SY003712;TS-02011;AM20050236;FT-0618719;FT-0695624;H0769;EN300-17313;M02899;J-513746;SR-01000639214-1;1-(TRIPHENYLMETHYL)PYRIDINIUMTETRAFLUOROBORATE;Q27273399;Z56917404;4AY;E5X

Chemical Property of 4-(Hydroxymethyl)benzoic acid

Chemical Property:

• Vapor Pressure: 2.03E-05mmHg at 25°C
• Melting Point: 182-185 °C(lit.)
• Refractive Index: 1.6
• Boiling Point: 347.4 °C at 760 mmHg
• PKA: 4.16±0.10(Predicted)
• Flash Point: 178.1 °C
• Density: 1.314 g/cm³
• Storage Temp.: 2-8°C
• Solubility.: DMSO, Methanol
• XLogP3: 0.9
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 152.047344113
• Heavy Atom Count: 11
• Complexity: 136

Purity/Quality:

99% ^*data from raw suppliers

4-Hydroxymethylbenzoic Acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-36-37/39

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C1=CC(=CC=C1CO)C(=O)O
• Uses: 4-(Hydroxymethyl)benzoic Acid is an intermediate in the synthesis of Eprosartan (E590100), a prototype of the imidazoleacrylic acid angiotensin II receptor antagonists used as an antihypertensive age nt. This linkage reagent for SPPS is essentially acid stable. It is useful in combination with Fmoc-amino acids. Its peptide esters are usually cleaved by basic or nucleophilic reagents, especially by ammonia in the preparation of peptide amides. 4-(Hydroxymethyl)benzoic Acid (Eprosartan USP Related Compound E) is an intermediate in the synthesis of Eprosartan (E590100), a prototype of the imidazoleacrylic acid angiotensin II receptor antagonists used as an antihypertensive agent.

Technology Process of 4-(Hydroxymethyl)benzoic acid

There total 58 articles about 4-(Hydroxymethyl)benzoic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

acetic acid (64-19-7,77671-22-8) + p-Toluic acid (99-94-5) → terephthalic acid (100-21-0) + 3-hydroxymethyl-benzoic acid (3006-96-0) + p-acetoxymethyl benzoic acid (15561-46-3) + 4-Carboxybenzaldehyde (619-66-9)

Guidance literature:

With N-hydroxyphthalimide; air; cobalt(II) acetate; manganese(II) acetate; at 150 ℃; for 3h; under 22800 Torr;

DOI:10.1002/1615-4169(20010226)343:2<220::aid-adsc220>3.0.co;2-n

Reference yield: 83.0%

p-xylylene glycol (589-29-7) → terephthalic acid (100-21-0) + 3-hydroxymethyl-benzoic acid (3006-96-0)

Guidance literature:

With tert.-butylhydroperoxide; copper(l) chloride; In decane; acetonitrile; at 20 ℃; for 6h;

DOI:10.1016/j.tetlet.2008.02.031

Reference yield: 82.0%

para-xylene (106-42-3) → terephthalic acid (100-21-0) + 3-hydroxymethyl-benzoic acid (3006-96-0) + 4-Carboxybenzaldehyde (619-66-9) + p-Toluic acid (99-94-5)

Guidance literature:

With N-hydroxyphthalimide; oxygen; manganese(II) acetate; cobalt(II) acetate; In acetic acid; at 100 ℃; for 14h; under 760 Torr; Further Variations:; Catalysts; Reagents; Solvents; Temperatures; ratio; Kinetics; Product distribution;

DOI:10.1002/1615-4169(20010226)343:2<220::aid-adsc220>3.0.co;2-n

upstream raw materials:

4-bromomethylbenzoic Acid

p-(chloromethyl)benzoic acid

p-methylbenzyl alcohol acetate

4-Cyanobenzyl alcohol

Downstream raw materials:

4-Methoxycarbonyl-α-chlor-hydrozimtsaeure-methylester

p-methoxymethylbenzoic acid methyl ester

allyl 4-hydroxymethylbenzoate

ethyl 4-(acetoxymethyl)benzoate

Refernces

• 1、 Bernhardt, Paul V.,Kilah, Nathan L.,Meacham, Andrew P.,Meredith, Paul,Vogel, Robert. "Immobilisation of electroactive macrocyclic complexes within titania films". . p. 2508 - 2515. Retrieved 2005.
• 2、 Li, Xinying,Mi, Tongge,Guo, Wenjing,Ruan, Zhongrui,Guo, Yu,Ma, Yan-Na,Chen, Xuenian. "KB3H8: An environment-friendly reagent for the selective reduction of aldehydes and ketones to alcohols". supporting information. p. 12776 - 12779. Retrieved 2021/12/10.
• 3、 Gao, Huanxin,He, Limin,Liu, Zhicheng,Wang, Yangdong,Xie, Zaiku. "Nitrogen doped carbon for Pd-catalyzed hydropurification of crude terephthalic acid: Roles of nitrogen species". . p. 33646 - 33652. Retrieved 2021/12/07.