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19261-06-4

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19261-06-4 Usage

General Description

Dibenzofuran-4-ol, also known as 4-hydroxydibenzofuran, is a chemical compound that belongs to the group of dibenzofurans. It is a white crystalline solid with a phenolic odor and is soluble in organic solvents. Dibenzofuran-4-ol is commonly used as a building block in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. It also has potential applications in materials science and as a precursor for the production of dyes and pigments. Additionally, it is known to have antioxidant and anti-inflammatory properties, making it a subject of interest in medicinal and cosmetic research. Despite its potential uses, dibenzofuran-4-ol is considered hazardous, and proper safety precautions should be followed when handling and working with this chemical.

Check Digit Verification of cas no

The CAS Registry Mumber 19261-06-4 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,9,2,6 and 1 respectively; the second part has 2 digits, 0 and 6 respectively.
Calculate Digit Verification of CAS Registry Number 19261-06:
(7*1)+(6*9)+(5*2)+(4*6)+(3*1)+(2*0)+(1*6)=104
104 % 10 = 4
So 19261-06-4 is a valid CAS Registry Number.
InChI:InChI=1/C12H8O2/c13-10-6-3-5-9-8-4-1-2-7-11(8)14-12(9)10/h1-7,13H

19261-06-4SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 17, 2017

Revision Date: Aug 17, 2017

1.Identification

1.1 GHS Product identifier

Product name dibenzofuran-4-ol

1.2 Other means of identification

Product number -
Other names 2-dibenzofuranol

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:19261-06-4 SDS

19261-06-4Synthetic route

4-methoxydibenzo[b,d]furan
41799-27-3

4-methoxydibenzo[b,d]furan

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
With boron tribromide In dichloromethane at -78 - 20℃;100%
potassium (dibenzo[b,d]furan-4-yl)trifluoroborate

potassium (dibenzo[b,d]furan-4-yl)trifluoroborate

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
With Oxone; water In acetone at 20℃; for 0.0833333h;97%
4-dibenzofurylboronic acid
100124-06-9

4-dibenzofurylboronic acid

dihydrogen peroxide
7722-84-1

dihydrogen peroxide

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
With ammonium bicarbonate In water at 20℃; for 2h; Schlenk technique;96%
4-dibenzofurylboronic acid
100124-06-9

4-dibenzofurylboronic acid

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
With dihydrogen peroxide In water at 20℃; for 0.0833333h;95%
With sodium hydroxide; dihydrogen peroxide In tetrahydrofuran at 20℃; for 24h;94%
With copper(II) ferrite; water; sodium hydroxide at 40℃; for 24h; Green chemistry;93%
dibenzofuran
132-64-9

dibenzofuran

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
Stage #1: dibenzofuran With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In hexanes; diethyl ether for 1h; Heating / reflux;
Stage #2: With boric acid tributyl ester In hexanes; diethyl ether at 0 - 20℃;
Stage #3: With dihydrogen peroxide In hexanes; diethyl ether; water at 0℃; for 1.5h; Heating / reflux;
81%
Stage #1: dibenzofuran With n-butyllithium; N,N,N,N,-tetramethylethylenediamine In diethyl ether; hexane for 1h; Heating;
Stage #2: With boric acid tributyl ester In diethyl ether; hexane at 20℃; for 1h;
Stage #3: With dihydrogen peroxide In diethyl ether; hexane; water for 1.5h; Heating;
71%
Stage #1: dibenzofuran With n-butyllithium In tetrahydrofuran at -78 - 40℃; for 18h;
Stage #2: With methylmagnesium bromide In tetrahydrofuran at -5 - 20℃; for 1h;
Stage #3: With hydrogenchloride; water; oxygen more than 3 stages;
47%
dibenzofuran
132-64-9

dibenzofuran

A

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

B

4,4'-bidibenzo[b,d]furan
86532-14-1

4,4'-bidibenzo[b,d]furan

Conditions
ConditionsYield
With n-butyllithium; diethyl ether anschl. mit Butylmagnesiumbromid in Aether und mit Sauerstoff;
2-chloro-dibenzofuran-4-ol
668454-81-7

2-chloro-dibenzofuran-4-ol

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
With palladium on activated charcoal; Lindlar's catalyst; ethanol
4-acetoxydibenzofuran
101762-27-0

4-acetoxydibenzofuran

S-benzylcysteine methyl ester
22728-88-7

S-benzylcysteine methyl ester

A

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

B

(+)-2-acetamido-3-benzylthiopropanoic acid methyl ester
77549-14-5

(+)-2-acetamido-3-benzylthiopropanoic acid methyl ester

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Rate constant;
4-acetoxydibenzofuran
101762-27-0

4-acetoxydibenzofuran

S-benzyl-L-cysteine ethyl ester
953-18-4

S-benzyl-L-cysteine ethyl ester

A

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

B

(R)-2-Acetylamino-3-benzylsulfanyl-propionic acid ethyl ester
26723-10-4

(R)-2-Acetylamino-3-benzylsulfanyl-propionic acid ethyl ester

Conditions
ConditionsYield
In dimethyl sulfoxide at 25℃; Rate constant;
phenol
108-95-2

phenol

A

2-hydroxydibenzofuran
86-77-1

2-hydroxydibenzofuran

B

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

C

2-Phenoxyphenol
2417-10-9

2-Phenoxyphenol

D

2,2'-dihydroxybiphenyl
1806-29-7

2,2'-dihydroxybiphenyl

Conditions
ConditionsYield
With oxygen In benzene at 499.84℃; for 0.0125h; Product distribution; Further Variations:; Reagents; Temperatures; slow combustion;
2-bromoanisole
578-57-4

2-bromoanisole

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / K2CO3; Cu2O / 2.5 h / Heating
2: 15 percent / Pd(OAc)3 / acetic acid / 7 h / Heating
3: 100 percent / BBr3 / CH2Cl2 / -78 - 20 °C
View Scheme
2-methoxyphenyl phenyl ether
1695-04-1

2-methoxyphenyl phenyl ether

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 15 percent / Pd(OAc)3 / acetic acid / 7 h / Heating
2: 100 percent / BBr3 / CH2Cl2 / -78 - 20 °C
View Scheme
phenol
108-95-2

phenol

cyclic dichloride of/the/ benzoic acid sulfinic acid-(2)

cyclic dichloride of/the/ benzoic acid sulfinic acid-(2)

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / K2CO3; Cu2O / 2.5 h / Heating
2: 15 percent / Pd(OAc)3 / acetic acid / 7 h / Heating
3: 100 percent / BBr3 / CH2Cl2 / -78 - 20 °C
View Scheme
2-chlorodibenzofuran
51230-49-0

2-chlorodibenzofuran

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: butyl lithium; diethyl ether; etheric butyl magnesium bromide solution / anschliessend mit Sauerstoff behandeln
2: palladium/calcium carbonate; ethanol
View Scheme
2-bromodibenzo[b,d]furan
86-76-0

2-bromodibenzo[b,d]furan

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: benzene; butyl lithium; diethyl ether / erneutes Versetzen mit 2-Brom-dibenzofuran- und Behandeln des Reaktionsgemisches mit festem Kohlendioxid und Aether.
2: butyl lithium; diethyl ether / anschliessend mit aether. Butylmagnesiumbromid-Loesung und mit Sauerstoff
View Scheme
Multi-step reaction with 2 steps
1: benzene; butyl lithium; diethyl ether / erneutes Versetzen mit 2-Brom-dibenzofuran- und Behandeln des Reaktionsgemisches mit festem Kohlendioxid und Aether.
2: butyl lithium; diethyl ether / anschl. mit Butylmagnesiumbromid in Aether und mit Sauerstoff
View Scheme
n-butyl magnesium bromide
693-03-8

n-butyl magnesium bromide

dibenzofuran
132-64-9

dibenzofuran

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

Conditions
ConditionsYield
With hydrogenchloride; n-butyllithium In diethyl ether
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

acetic anhydride
108-24-7

acetic anhydride

4-acetoxydibenzofuran
101762-27-0

4-acetoxydibenzofuran

Conditions
ConditionsYield
With sulfuric acid for 4h;100%
With sulfuric acid
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

methyl iodide
74-88-4

methyl iodide

4-methoxydibenzo[b,d]furan
41799-27-3

4-methoxydibenzo[b,d]furan

Conditions
ConditionsYield
With potassium carbonate In acetone for 18h; Heating / reflux;100%
With potassium carbonate In acetone Reflux;99%
With potassium carbonate In acetone for 11h; Heating;93%
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

N,N-diethylcarbamyl chloride
88-10-8

N,N-diethylcarbamyl chloride

dibenzofuan-4-yl diethylcarbamate

dibenzofuan-4-yl diethylcarbamate

Conditions
ConditionsYield
With pyridine at 85℃; for 15h;98%
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

propargyl bromide
106-96-7

propargyl bromide

4-(2-propynyloxy)dibenzo[b,d]furan

4-(2-propynyloxy)dibenzo[b,d]furan

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 2h;93%
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

2,6-difluoroiodobenzene
13697-89-7

2,6-difluoroiodobenzene

C30H17IO4

C30H17IO4

Conditions
ConditionsYield
With potassium carbonate In 1-methyl-pyrrolidin-2-one for 6h; Inert atmosphere; Reflux;93%
Cyclopentyl bromide
137-43-9

Cyclopentyl bromide

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

4-cyclopentyloxydibenzo[b,d]furan
685873-63-6

4-cyclopentyloxydibenzo[b,d]furan

Conditions
ConditionsYield
With sodium hydride92%
With potassium carbonate In N,N-dimethyl-formamide at 50 - 100℃; for 4 - 5h;90%
Stage #1: 4-hydroxydibenzofuran With potassium carbonate In N,N-dimethyl-formamide at 80℃; for 0.5h;
Stage #2: Cyclopentyl bromide In N,N-dimethyl-formamide at 80℃; for 3h;
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

4-cyclopropylmethoxydibenzo[b.d]furan

4-cyclopropylmethoxydibenzo[b.d]furan

Conditions
ConditionsYield
Stage #1: 4-hydroxydibenzofuran With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.0833333h;
Stage #2: cyclopropylcarbinyl bromide In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 1.16667h;
90%
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

ethyl iodide
75-03-6

ethyl iodide

4-ethoxy-dibenzofuran
685873-95-4

4-ethoxy-dibenzofuran

Conditions
ConditionsYield
Stage #1: 4-hydroxydibenzofuran With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.0833333h;
Stage #2: ethyl iodide In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 1.16667h;
82%
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

methanesulfonyl chloride
124-63-0

methanesulfonyl chloride

dibenzo[b,d]furan-4-yl methanesulfonate
1314564-31-2

dibenzo[b,d]furan-4-yl methanesulfonate

Conditions
ConditionsYield
With pyridine In dichloromethane at 0 - 20℃; Inert atmosphere;77%
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

trifluoromethylsulfonic anhydride
358-23-6

trifluoromethylsulfonic anhydride

trifluoromethanesulfonic acid dibenzofuran-4-yl ester

trifluoromethanesulfonic acid dibenzofuran-4-yl ester

Conditions
ConditionsYield
With triethylamine In dichloromethane at 0 - 20℃; for 2h; Inert atmosphere;73%
2-methyl-8-quinolinol
826-81-3

2-methyl-8-quinolinol

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

aluminum isopropoxide
555-31-7

aluminum isopropoxide

C32H23AlN2O4

C32H23AlN2O4

Conditions
ConditionsYield
Stage #1: 2-methyl-8-quinolinol; aluminum isopropoxide In ethanol for 2h; Reflux; Inert atmosphere;
Stage #2: 4-hydroxydibenzofuran In ethanol Reflux;
62%
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

3-bromodibenzofuran-4-ol

3-bromodibenzofuran-4-ol

Conditions
ConditionsYield
With N-Bromosuccinimide In dichloromethane at -12 - 20℃; Inert atmosphere; regioselective reaction;62%
With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃;
With bromine; acetic acid at 0 - 20℃; for 5h;
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

chloroform
67-66-3

chloroform

4-hydroxydibenzofuran-3-carboxaldehyde
635305-19-0

4-hydroxydibenzofuran-3-carboxaldehyde

Conditions
ConditionsYield
Stage #1: 4-hydroxydibenzofuran; chloroform With sodium hydroxide In water at 60 - 65℃; Reimer-Tiemann formylation;
Stage #2: In water at 90℃; for 0.25h;
13%
diethyl sulfate
64-67-5

diethyl sulfate

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

4-ethoxy-dibenzofuran
685873-95-4

4-ethoxy-dibenzofuran

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

2-chloroethyl tosylate
80-41-1

2-chloroethyl tosylate

4-(2-chloro-ethoxy)-dibenzofuran

4-(2-chloro-ethoxy)-dibenzofuran

Conditions
ConditionsYield
With sodium hydroxide
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

benzene diazonium chloride
100-34-5

benzene diazonium chloride

1-phenylazo-dibenzofuran-4-ol

1-phenylazo-dibenzofuran-4-ol

Conditions
ConditionsYield
With potassium hydroxide
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

dimethyl sulfate
77-78-1

dimethyl sulfate

4-methoxydibenzo[b,d]furan
41799-27-3

4-methoxydibenzo[b,d]furan

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

dimethyl sulfate
77-78-1

dimethyl sulfate

1,3-dibromo-4-methoxy-dibenzofuran

1,3-dibromo-4-methoxy-dibenzofuran

Conditions
ConditionsYield
With bromine
n-butyllithium
109-72-8, 29786-93-4

n-butyllithium

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

diethyl ether
60-29-7

diethyl ether

methylammonium carbonate
15719-64-9, 15719-76-3, 97762-63-5

methylammonium carbonate

benzene
71-43-2

benzene

6-hydroxy-dibenzofuran-4-carboxylic acid
501009-01-4

6-hydroxy-dibenzofuran-4-carboxylic acid

4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

4-aminodibenzofuran
50548-43-1

4-aminodibenzofuran

Conditions
ConditionsYield
With ammonium hydroxide; sodium disulfite at 195℃;
With ammonium chloride; zinc(II) chloride at 280℃;
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

dibenzofuran-1,4-dione
54808-25-2

dibenzofuran-1,4-dione

Conditions
ConditionsYield
With sodium periodate; acetic acid unter Lichtausschluss;
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

1-chloro-4-hydroxydibenzofuran
41799-31-9

1-chloro-4-hydroxydibenzofuran

Conditions
ConditionsYield
With sulfuryl dichloride; chloroform; iodine
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

1-bromodibenzofuran-4-ol
873974-43-7

1-bromodibenzofuran-4-ol

Conditions
ConditionsYield
With bromine; acetic acid
Multi-step reaction with 3 steps
1: 1H-imidazole / dichloromethane / 18 h / 20 °C / Inert atmosphere
2: N-Bromosuccinimide / tetrahydrofuran / 17 h / 20 °C / Inert atmosphere
3: cesium fluoride / tetrahydrofuran / 19 h / 20 °C / Inert atmosphere
View Scheme
4-hydroxydibenzofuran
19261-06-4

4-hydroxydibenzofuran

3-chloro-4-hydroxydibenzofuran
51596-34-0

3-chloro-4-hydroxydibenzofuran

Conditions
ConditionsYield
With tetrachloromethane; chlorine; iron
With chlorine In tetrachloromethane Heating;50 mg

19261-06-4Relevant articles and documents

DNA-dependent protein kinase (DNA-PK) inhibitors. synthesis and biological activity of quinolin-4-one and pyridopyrimidin-4-one surrogates for the chromen-4-one chemotype

Cano, Céline,Barbeau, Olivier R.,Bailey, Christine,Cockcroft, Xiao-Ling,Curtin, Nicola J.,Duggan, Heather,Frigerio, Mark,Golding, Bernard T.,Hardcastle, Ian R.,Hummersone, Marc G.,Knights, Charlotte,Menear, Keith A.,Newell, David R.,Richardson, Caroline J.,Smith, Graeme C. M.,Spittle, Ben,Griffin, Roger J.

, p. 8498 - 8507 (2010)

Following the discovery of dibenzo[b,d]thiophen-4-yl)-2-morpholino-4H- chromen-4-one (NU7441) (Leahy, J. J. J.; Golding, B. T.; Griffin, R. J.; Hardcastle, I. R.; Richardson, C.; Rigoreau, L.; Smith, G. C. M. Bioorg. Med. Chem. Lett. 2004, 14, 6083-6087) as a potent inhibitor (IC50 = 30 nM) of DNA-dependent protein kinase (DNA-PK), we have investigated analogues in which the chromen-4-one core template has been replaced by aza-heterocyclic systems: 9-substituted 2-morpholin-4-ylpyrido[1,2-a]pyrimidin-4-ones and 8-substituted 2-morpholin-4-yl-1H-quinolin-4-ones. The 8- and 9-substituents were either dibenzothiophen-4-yl or dibenzofuran-4-yl, which were each further substituted at the 1-position with water-solubilizing groups [NHCO(CH 2)nNR1R2, where n = 1 or 2 and the moiety R1R2N was derived from a library of primary and secondary amines (e.g., morpholine)]. The inhibitors were synthesized by employing a multiple-parallel approach in which the two heterocyclic components were assembled by Suzuki-Miyaura cross-coupling. Potent DNA-PK inhibitory activity was generally observed across the compound series, with structure activity studies indicating that optimal potency resided in pyridopyrimidin-4- ones bearing a substituted dibenzothiophen-4-yl group. Several of the newly synthesized compounds (e.g., 2-morpholin-4-yl-N-[4-(2-morpholin-4-yl-4-oxo-4H- pyrido[1,2-a]pyrimidin-9-yl)dibenzothiophen-1-yl]acetamide) combined high potency against the target enzyme (DNA-PK IC50 = 8 nM) with promising activity as potentiators of ionizing radiation-induced cytotoxicity in vitro.

Blacklight-Induced Hydroxylation of Arylboronic Acids Leading to Hydroxyarenes Using Molecular Oxygen and Tetrabutylammonium Borohydride

Kawamoto, Takuji,Ryu, Ilhyong

, (2021/09/06)

A new simple protocol for the conversion of arylboronic acids to hydroxyarenes was achieved using molecular oxygen in the presence of tetrabutylammonium borohydride under blacklight irradiation (360 nm). A radical chain mechanism in which a superoxide ion (O2?.) plays a key role is proposed.

A practical method for preparation of phenols from arylboronic acids catalyzed by iodopovidone in aqueous medium

Dong, Bin,Ke, Yanxiong,Lu, Guangying,Ren, Jiangmeng,Ren, Yaoyao,Zeng, Bu-Bing,Zhou, Bin

, (2019/09/06)

A novel and efficient strategy for the ipso-hydroxylation of arylboronic acids to phenols has been developed using inexpensive, readily available, air-stable water-soluble povidone iodine as catalyst and aqueous hydrogen peroxide as oxidizing agent. The reactions were performed at room temperature under metal-, ligand- and base-free condition in a short reaction time. The corresponding substituted phenols were obtained in moderate to good yields by oxidative hydroxylation of arylboronic acids in aqueous medium.

Visible-Light-Mediated Aerobic Oxidation of Organoboron Compounds Using in Situ Generated Hydrogen Peroxide

Weng, Wei-Zhi,Liang, Hao,Zhang, Bo

supporting information, p. 4979 - 4983 (2018/08/24)

A simple and general visible-light-mediated oxidation of organoboron compounds has been developed with rose bengal as the photocatalyst, substoichiometric Et3N as the electron donor, as well as air as the oxidant. This mild and metal-free protocol shows a broad substrate scope and provides a wide range of aliphatic alcohols and phenols in moderate to excellent yields. Notably, the robustness of this method is demonstrated on the stereospecific aerobic oxidation of organoboron compounds.

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